Yeah, but there are so many ultra-wealthy, ultra-famous men who wife and date women who I wouldn't even bother to buy a drink for. The only guy I can think of off the top of my head who did something similar to Drake was Dan Bilzerian had Wendy Fiore on his private jet to Italy like 7-8 years ago; but that was the only huge-chested woman I saw him do it with. Jamie Foxx had Martha Ethio on a yacht/boat a couple years back. But other than that, it seems like most celebrity/famous men don't like huge breasts that much.
Also, from what Sierra said on one of her lives, he actually contacts them on a different IG account unconnected to his main, and communicates with them through there. I guess he must send them a selfie with a date or holding a current newspaper to prove it's actually him lol